反应详情

温度

0 °C

To the THF (2 ml) solution of lithium aluminum hydride (68 mg, 1.80 mmol), aluminum chloride (240 mg, 1.80 mmol) was added under ice cooling. After stirring for 10 minutes at 0° C., THF (4 ml) solution of 5-[4-(4-methoxyphenyl)piperazin-1-yl]-4,6,7-trimethyl-1-benzofuran-3(2H)-one (220 mg, 0.600 mmol) synthesized in Reference example 109 was added. The mixture was stirred for 3 hours under reflux. After cooling to room temperature, water was added to the reaction solution, and 0.5 N aqueous solution of sodium hydroxide was further added to the reaction solution. The mixture was stirred for 30 minutes at room temperature and extracted with ethyl acetate-diethyl ether (1/1) mixture solvent. The extract solution was washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (20 ml), added with 10%-palladium carbon (comprising 50% moisture, 200 mg), and then the mixture was stirred at 60° C. for 15 hours under hydrogen atmosphere. After cooling to room temperature, palladium carbon was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-80/20) to obtain the title compound 35 mg (yield 17%).

1. additionwas added
2. stirringThe mixture was stirred for 3 hours
3. temperatureunder reflux
4. temperatureAfter cooling to room temperature
5. additionwas further added to the reaction solution
6. stirringThe mixture was stirred for 30 minutes at room temperature
7. extractionextracted with ethyl acetate-diethyl ether (1/1) mixture solvent
8. washThe extract solution was washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure
11. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
12. additionadded with 10%-palladium carbon (comprising 50% moisture, 200 mg)
13. stirringthe mixture was stirred at 60° C. for 15 hours under hydrogen atmosphere
14. temperatureAfter cooling to room temperature
15. custompalladium carbon was removed by filtration
16. concentrationthe filtrate was concentrated under reduced pressure
17. customThe residue was purified by silica gel chromatography (hexane-ethyl acetate 95:5-80/20)